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The Future Belongs to the Empathetic Seller

6 min readMay 16, 2018

“Nobody cares how much you know, until they know how much you care.” – Theodore Roosevelt

People Buy From People They Like Trust

“People buy from people they like” – you’ve all heard this one before. Certainly likability is a good characteristic to have, but the truth is that people buy from people they TRUST.

But here’s the cold, hard truth: Only 18% of buyers trust and respect salespeople.

Holy cow – you guys, that’s really bad. Picture the last 100 people you and your team have tried to sell to, all together, in one massive conference room. Now tell 82 of them to leave the room. Only those remaining 18 actually trusted and respected you. Ouch.

Modern buyers need a Sherpa, not a Sales Rep. They need someone who understands where they want to go, has walked the path before, and can be trusted to lead them through what can often be a treacherous and bumpy journey. There are political landmines, procurement booby traps, high stakes decisions to turn left or turn right – and you better believe they need to have full and complete trust in the person leading them through it all.

The key to becoming a Sherpa? To earning deep, meaningful and long-lasting trust from those you interact with? Empathy.  

Still don’t believe me? It’s time for some real talk from real buyers.

In the fantastic series “How I Buy” by Steve Woods of Nudge.ai, you’ll find direct quotes from many of the people you spend your days trying to sell to. Here’s just a sample of what you’ll find:

“I generally try to limit time with reps from vendors…. The discussion on my business, my top 3 initiatives, etc. is just a waste of my time.” – Meghan Eisenberg, CMO of MongoDB

Did you catch that? “waste of my time”It’s harsh, I know – but it’s the truth. Most buyers agree that interactions with salespeople rarely deliver value. And as a result, they avoid interacting with salespeople.

Why is this the case? You guessed it. Because buyers don’t trust salespeople. By and large, they don’t believe their – and your – best interests are aligned. Most would even prefer to look to total strangers sharing their opinions on G2Crowd and Quora instead of taking a sales call.

So how do we fix this? How can you ensure that you are the exception to the rule? Time to up your Empathy game.

“The best sales people ask good questions, listen, and adapt to our process.” – Jay Hedges, SVP Revenue, Uberflip

A skilled Empathetic Seller understands their prospects and their business at a deep level. They put themselves in their customer’s seat, ask many and meaningful questions – not just because they were covered in “Sales Discovery” training, but also because they are genuinely curious and actually interested in the answers.

Empathy Builds Trust

Business Handshake Trust SherpaEmpathy is an emotional intelligence skill, defined as the ability to understand and share the feelings of another. It’s the Sherpa who isn’t just going to tell you how to get to the top of the mountain but is also going to wrestle on your heavy backpack, lace up your dirty hiking boots and put on your sweaty hat so they can feel what it’s like in your shoes (literally).

Too many sellers today are focused on moving prospects through a sales process and aren’t stopping to spend the time trying to consider or understand their buyer’s perspectives, experiences or motivations. If you try to take the short cut and skip an empathetic approach, you will never gain enough trust to be in a position to influence others.

“The best salespeople are the ones who realize the incredible power of empathy and can understand the other party without them explicitly stating it.” – Gary Vaynerchuk

And yet, in all my years of sales training, onboarding, role playing and coaching, there has been a striking lack of focus on the importance of empathy in selling – and along with that, the skills, techniques and incorporation of empathy into your working style.

It’s time for a purposeful focus on developing our collective aptitude for empathetic selling.

Three Ways to Up-level your Empathetic Selling Today

1.   Listen and Observe. Call it active listening, call it being present, call it whatever you want – but PLEASE just do it. Stop focusing on what you’re going to say next, what your “objective” is for the call or meeting, just for a moment – tune in, pay attention, get interested, ask real questions, listen to the answers and engage in a meaningful conversation with those you are trying to sell to. (then, I promise you, you will be better equipped to achieve what you’re ultimately trying to do…).

Test yourself along the way – ask and confirm with the person you’re talking to “this is what I heard you say, this is what I understand the situation and objective to be, do I have that right?”

2.  Put yourself in their shoes.

“You never really understand a person until you consider things from his point of view . . . until you climb into his skin and walk around in it.” – Atticus Finch, To Kill a Mockingbird

Seeing the world from their perspective is the most powerful position to accurately align your interests. Have a product or solution you think will benefit them? Test that hypothesis – imagine you are in their chair. What questions or concerns would you have? What benefits, near term and long term, would you achieve? Let that perspective inform how you position your solution and how you collaborate on moving ahead towards a mutually beneficial outcome.

3.  Incorporate the insights you glean from doing #1 and #2 into your conversations with the people you’re talking to! Now that you’ve done the work to listen, observe and understand their point of view, demonstrate to them that you’ve done just that. Here’s how that might play out.

Say you have a game changing product that will address your prospects most burning need. But, using your product also requires the right resources, time and some internal process changes. The seller who leverages empathy here (instead of just trying to close) will pause and focus on what it’s like in the buyer’s seat, taking the time to see things from their point of view.

“Andrew, there seems to be a fit here – our solution could definitely address many of the pains you’ve shared with me. If I put myself in your shoes, a few concerns I might have are related to the time and resources needed to get up and running. Are these worthwhile subjects to spend a little time talking through?”

I promise you, this is rare among sellers today and you’ll immediately gain a few trust points from your prospect. They’ll be relieved you actually “get” them.

During your next sales conversation, you’ll still need to apply your tried and true hard selling skills. They exist for a reason. But to elevate your game and establish a meaningful relationship, begin incorporating those soft skills. Look at things through your prospect’s eyes, pay attention to their communication style, the words they use and the concerns they surface. By doing so, you will strengthen your emotional connection and develop an even deeper understanding of the situation.

Build a relationship based on trust and understanding and you will be rewarded with a position of influence.

Ignore developing and leveraging those skills and you’ll be the one left wandering the mountain looking for a Sherpa to save you.